What it’s Really Like to Star (and Succeed) on Apple Music’s New Show Planet of the Apps

When I left my (paying) job to work full time on my side project, Dote, I made a deal with myself. If I was going to do this, I had to give it everything I had. Early mornings, late nights, weekends, holidays. Even when I didn’t feel like it, even when I was way outside of my comfort zone. I was all in.

When the opportunity to pitch Dote on Apple Music’s new series, Planet of the Apps, came across my inbox, I knew it was the kind of thing I had to embrace. So far my Year of Yes hadn’t led me astray.

Waiting for the flight from SFO to LA, where I’d give my first pitch to Jessica Alba, Gwyneth Paltrow, Gary Vaynerchuk and will.i.am, the advisors for Planet of the Apps, I spotted a hodgepodge group of men and women, scrolling through their iPhones, speaking to each other in hushed voices, some bespectacled, some vitamin D deficient, all a little under slept. I recognized my fellow ilk immediately. I watched them from afar until we got to our hotel in the heart of Hollywood. “Are you here for that, uh, Apple thing?” I asked. The NDAs regarding our participation in the show left little wiggle room to chat freely. “Yes we are!” they exclaimed. Fast friends.

Some stuttered and stumbled and blanked, but we all finished our pitches. Halfway through, Gwyneth’s kids showed up on-set wanting to try the escalator. It looked like a lot of fun to ride if you didn’t have to give a perfectly timed startup pitch at the same time. Happily, I made it through the first round with Gwyneth Paltrow as my advisor.

What I hope the show captures but was clear to all of us on set, is how dedicated the advisors were to the process and to us as founders. Will.i.am was genuinely heartbroken when someone wasn’t chosen for the accelerator. He and Gary V. spoke with a group of us for hours after filming about their experiences fundraising and building companies.

After wrapping up, the developers who pitched that day went out for drinks. We didn’t really know what to think of it all. There were companies that were only ideas, companies that had already raised tens of millions of dollars of funding, and everything in between. Despite our differences, the camaraderie was immediate. Almost all of us had left a path more stable and secure to pursue our pipedream. We were from all over, from all professional backgrounds and from all walks of life, but what we had in common was a belief that we owed it to ourselves to see if we could make it striking out on our own.

With the pitch done, we were back on our own, with 6 weeks to prepare for the VC pitch at Lightspeed Venture Partners. When I arrived home in SF, the bodysuit Jessica Alba demanded I order during my presentation was waiting at my doorstep (Jessica, let me know if you still want it!)

My first meeting with Gwyneth at the Goop office was all business. Even though I’ve met my share of successful advisors and founders in Silicon Valley, I was still pretty nervous to meet with the Goop team in LA. I met with the producer at a coffee shop a block away before walking over to see the office for the first time. It did not disappoint. Goop is the hippest-without-trying-to-be-hip headquarters I’ve ever seen — invisible from the street. Everyone who works there was well-prepared and looked impeccable. (Also—Coldplay was playing in the background!)

Gwyneth and I walked through an old pitch deck and she quizzed me on our metrics. “You have GOT to get LTV higher (loan to value ratio),” she said. “I know,” I admitted. Then she smiled and said, “If Lightspeed doesn’t want to do this, we’ll go find someone who will.” Surreal. But the meeting put me at ease. Gwyneth believed in Dote as much as I did.

Right before Christmas I emailed Gwyneth asking if she could reach out to influencers on Dote’s behalf to ask if they wanted to get featured in our app. “The only problem is, they’ll never believe it is you,” I said. “Can you send me a Dote hat so I can take a selfie to send with the note?” she asked. “It’s on its way,” I replied.

Week after week, not only was my relationship with Gwyneth and the Goop team growing, but so was my relationship with the other developers and producers. By the time our VC pitches were scheduled, we had all seen each other’s great progress and were rooting for one another.

My call time for the VC pitch was 6 AM. It was still dark when we arrived at the co-working space where we would present to Lightspeed. I was slated for the afternoon, but then we got word that all of Gwyneth’s pitches were moved to the morning. It was go time.

Gwyneth and I showed up in almost the same outfit, her in all green and me in all black. We’d already been getting comments about our matching blonde hair, so in a way it felt kind of fitting. We’d been absorbed in the same project together for weeks. I’d been watching order after order come in on Dote from Gwyneth’s account and I’d become a Goop addict in the meantime, so at that point we were really channeling each other’s vibes. (Can I say that about Gwyneth Paltrow?)

Our pitch went just how we’d planned it. When I received the VC offer I was over the moon, but I hesitated because I was worried about dilution. You can see my reticence on the show! What you didn’t see was Gwyneth coaching me on taking the offer. The cameras were in our face but she pulled off her mic and whispered in my ear her percentage ownership of Goop after every fundraising round. “Baby Girl, the pie just gets bigger,” she said. I knew she was right.

I also wanted to get a hold of our board member and lead investor Michael Dearing before accepting anything, even verbally. Standing outside of the pitch room Gwyneth and I were frantically trying to call him to get his advice. He wasn’t picking up. She looked at me and said, “I think it’s just you and me Baby Girl.” It was! So I said, “Let’s do this.”

We went back and forth into the room with Lightspeed about five times. Over lunch, I received a request from them for some additional numbers concerning our spend and revenue, cost of acquiring new customers and the like. I frantically did my analysis in the holding area. I guess they liked what they saw!

We had some downtime before our post-pitch interview. Gwyneth told me about some of the challenges she was facing at the moment—her upcoming board meeting and some challenges they’d had procuring enough inventory to meet demand. We got personal too. I asked her if she missed acting. She said that she had achieved the pinnacle of success of acting at such an early age in winning an Oscar, and that she felt something in her that needed to see what else she could do. I recognized that feeling in myself.

Once the interview began, I said to the camera, “If I can do this, I think anybody can.” Gwyneth started laughing in the seat next to me and said, “That is not true. It’s so nice of you to say, but that’s not true.” It was a moment that will always stand out for me. This was the vote of confidence that made me feel like I’m the one to make Dote the enormous business I know it can be.

And just like that, filming was over. The developers went out for drinks that night. Spirits were mixed, but I think everyone was glad the long day was done. We all took a selfie together and sent it to Gwyneth. She texted back, “I wish I were there!” We did too.